Pyrrolidinol derivatives

The strategy described here explains the different possibilities of enzymatic ammonolysis and aminolysis reaction for resolution of esters or preparation of enantiomerically pure amides, which are important synthons in organic chemistry. This methodology has been also applied for the synthesis of pyrrolidinol derivatives that can be prepared via enzymatic ammonolysis of a polyfunctional ester, such as ethyl ( )-4-chloro-3-hydroxybutanoate [30]. In addition, it is possible in the resolution of chiral axe instead of a stereogenic carbon atom. An interesting enzymatic aminolysis of this class of reaction has been recently reported by Aoyagi et al. [31[. The side chain of binaphthyl moiety plays an important role in the enantiodis-crimination of the process (Scheme 7.14). 

The total synthesis of (— )-nummularine-F (163), a 4(14)-amphibine-F-type cyclopeptide alkaloid, from D-serine was accomplished in 25 steps and an overall yield of 0.48%. This approach includes a stereoselective synthesis of a cw-2-(hydroxymethyl)-3-pyrrolidinol derivative, the inversion of the cjs-3-hydroxyl function to the desired... 

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